Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)‐Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(2), С. 512 - 524

Опубликована: Ноя. 4, 2020

Abstract A regioselective and chemodivergent synthetic approach for azulenolactones azulenolactams as a new scaffold was demonstrated through Rh(III)‐catalyzed reaction of N ‐methoxyazulene‐1‐carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act precursor secondary carbene described, leading to the selective formation bearing two substituents on newly introduced double bond. This method functionalization less reactive 2‐position azulene overcome natural reactivity. magnified image

Язык: Английский

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Desymmetrization of meso-Dicarbonatecyclohexene with β-Hydrazino Carboxylic Esters via a Pd-Catalyzed Allylic Substitution Cascade

Organic Letters, Год журнала: 2020, Номер 22(22), С. 8836 - 8841

Опубликована: Ноя. 10, 2020

The desymmetrization of meso-dicarbonatecyclohexene with β-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction chiral hexahydrocinnoline derivatives high performance. Mechanistic studies reveal that reaction exploits pathway different from our previous work and first nitrogen nucleophilic process is rate-determining step. protocol could be conducted on gram scale without any loss catalytic behavior, corresponding hexahydrocinnolines can undergo diverse transformations.

Язык: Английский

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Condition-Dependent Selective Synthesis of Indolo[1,2-c]quinazolines and Indolo[3,2-c]quinolines from 2-(1H-Indol-2-yl)anilines and Sulfoxonium Ylides

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(15), С. 9815 - 9828

Опубликована: Июль 15, 2022

In this paper, a selective synthesis of indolo[1,2-c]quinazolines and indolo[3,2-c]quinolines through the cascade reactions 2-(1H-indol-2-yl)anilines with sulfoxonium ylides is presented. The formation products involves generation carbene species from ylide its N–H bond insertion reaction 2-(1H-indol-2-yl)aniline followed by deoxygenative imine formation, intramolecular N– or C– nucleophilic addition aromatization. This switchable was condition-dependent. presence K2CO3 in CH3CN, mainly furnished indolo[1,2-c]quinazolines. HOAc dioxane, it selectively afforded indolo[3,2-c]quinolines. addition, direct C–H/N–H functionalization obtained provides convenient access to polycyclic heteroaromatic compounds. These novel protocols have advantages such as readily accessible substrates, easily tunable selectivity, good compatibility diverse functional groups, use air cost-free sustainable oxidant.

Язык: Английский

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Copper-Catalyzed [4+1+1] Annulation of Ammonium Salts and Anthranils: Synthesis of 2,3-Diaroylquinolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7446 - 7454

Опубликована: Май 15, 2024

A copper(I)-catalyzed protocol is developed for the synthesis of various 2,3-diaroylquinolines starting from achiral ammonium salts and anthranils through [4+1+1] annulation. Using copper(I) chloride as sole catalyst, this reaction featured with easily available materials, broad substrate scope, good yields simple conditions.

Язык: Английский

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Annulation-induced hidden reactivity of N-(2-ethynylaryl)-1,2,3-triazoles to cinnolines under microwave irradiation

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Март 1, 2025

Язык: Английский

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